The debate over Hypothetical Syllogism is locked in stalemate. Although putative natural language counterexamples to Hypothetical Syllogism abound, many philosophers defend Hypothetical Syllogism, arguing that the alleged counterexamples involve an illicit shift in context. The proper lesson to draw from the putative counterexamples, they argue, is that natural language conditionals are context-sensitive conditionals which obey Hypothetical Syllogism. In order to make progress on the issue, I consider and improve upon Morreau’s proof of the invalidity of Hypothetical Syllogism. The improved proof relies upon the semantic claim that conditionals with antecedents irrelevant to the obtaining of an already true consequent are themselves true. Moreover, this semantic insight allows us to provide compelling counterexamples to Hypothetical Syllogism that are resistant to the usual contextualist response